Lubricating oil composition

ABSTRACT

LUBRIATING OIL FOR TWO-CYCLE OR ROTARY ENGINE WHICH EMPLOY A LUBRICATING OIL-FUEL MIXTURE, CONTAINING THE POLYMERIC REACTION PRODUCT OF AN ALIPHATIC AMINE AND AN EPIHALOHYDRIN COMPOUND.

United States Patent 3,813,228 LUBRICATING OIL COMPOSITION Edward M.Geiser, Downers Grove, Ill., assignor to Universal Oil Products Company,Des Plaines, Ill. No Drawing. Filed July 17, 1972, Ser. No. 272,585 Int.Cl. C101 1/10 US. Cl. 44-58 Claims ABSTRACT OF THE DISCLOSURELubricating oil for two-cycle or rotary engines which employ alubricating oil-fuel mixture, containing the polymeric reaction productof an aliphatic amine and an epihalohydrin compound.

BACKGROUND OF THE INVENTION Lubricating oil used for two-cycle enginesis admixed with the fuel and charged into the combustion chamber of theengine. It, also, has been proposed to utilize the mixture of thelubricating oil and fuel in rotary type engines. Both of these enginesmay be of the air or water cooled design. The practice of utilizing amixture of the lubricating oil and fuel (gasoline) finds application inmarine engines, outboard engines, snowmobiles, golf carts, chain saws,compact automobiles, etc.

Because the lubricating oil is mixed with the fuel and charged inadmixture into the combustion zone, the problems encountered in theefficient operation of the engine appear to be more complicated thanencountered in systems in which the fuel and lubricating oil aresupplied separately and kept substantially isolated from each other.While some of the problems are common to both types of engines, it isapparent that different chemical and physical phenomena are encounteredwhen the lubricating oil and fuel are supplied as a mixture into thecombustion zone.

It is important to protect the lubricity properties of the lubricatingoil to avoid seizure occurring and interrupting operation of the engineand/or breakage of the engine parts. It is, also, important to maintainengine cleanliness and avoiding spark plug fouling, deposit formation oncylinder walls, exhaust ports, in the mufiler system, etc. In rotarytype engines, undue wear adversely affects the seals, with the resultantleakage and inefiicient engine operation. With the use of leaded fuels,these problems become even more complicated.

DESCRIPTION OF THE INVENTION In accordance with the present invention,the lubricity properties and engine cleanliness are improved byincorporating a particular polymeric reaction product in the lubricatingoil.

In one embodiment, the present invention relates to a lubricating oilfor two-cycle or rotary engines which employ lubricating oil-fuelmixture containing, as an additive to improve lubricity and enginecleanliness, from about 0.5% to about 10% by weight of the polymericreaction product, formed at a temperature of from about 70 to about 300F., of from 1 to 2 mole proportions of a primary or secondary aliphaticamine with from 1 to 1.5 mole proportions of an epihalohydrin compound.

In a particularly preferred embodiment, the polymeric reaction productis prepared in a parafiinic and an aromatic solvent. For example, in apreferred embodiment, the polymeric reaction product is prepared as a30% to 70% and more particularly 40% to 60% solution in an aromaticsolvent and the resulting solution then is commingled with a paraffinoil in an amount to comprise from about 10% to about 30% and preferablyfrom about to about 25% by weight of the first mentioned solution andfrom about 70% to about 90% and preferably 75% ice to about by weight ofthe paraffin oil. By utilizing the mixed solvents, satisfactorysolubility of the polymeric reaction product is obtained in thelubricating oil and in the subsequent mixture of lubricating oil andfuel. It is understood that the mixed solvents may be commingled withthe polymeric reaction product in any suitable manner, includingone-step admixture or sequential addition of the different solvents.

In another embodiment, the present invention relates to the method ofoperating a spark ignition two-cycle engine or a spark ignition rotaryengine, wherein lubricating oil and fuel are charged in admixture andpassed into the combustion chamber of said engine, which comprisesoperating said engine on the lubricating oil-fuel mixture containing thepolymeric reaction product herein set forth.

The polymeric reaction product for use in the present invention isformed by reacting a primary or secondary aliphatic amine with anepihalohydrin compound. The aliphatic amine may be a mono or polyamine.In a particularly preferred embodiment, the amine contains from about 12to about 40 carbon atoms.

In a preferred embodiment, the amine is an N-aliphatic polyamine andmore particularly an N-alkyl-diaminoalkane. Especially preferred areN-alkyl-1,3-diamiuopropanes in which the alkyl group contains at least12 carbon atoms and more particularly from 12 to about 40 carbon atoms.Illustrative examples include N-dodecyl-1,3-diaminopropane, N-tridecyl-1 ,Z-diaminopropane, N-tetradecyl- 1, 3-diaminopropane,N-pentadecyl-1,3-diaminopropane, N-hexadecyll ,3-diaminopropane,N-heptadecyl-l ,3-diaminopropane, N-octadecyll ,3-diamino propane,N-nonadecyl-1,3-diaminopropane, N-eicosyl-1,3-diaminopropane,N-heneicosyl-1,3-diaminopropane, N-docosyl- 1 ,3-diaminopropane,N-tricosyl-1,3-diaminopropane, N-tetracosyl-1,3-diaminopropane,N-pentacosyll ,3-diaminopropane, N-hexacosyl-l ,3-diarninopropane,N-heptacosyl-1,3-diaminopropane, N-octacosyl-1,3-diaminopropane,N-nonacosyl-1,3-diaminopropane, N-tricontyl-1,3-diaminopropane,N-hentriacontyl-1,3-diaminopropane, N-dotriacontyl-1,3-diaminopropane,N-tritriacontyl-1,3-diamiuopropane,N-tetratriacontyl-1,3-diaminopropane,N-pentatriacontyl-1,3-diaminopropane,N-hexatriacontyl-1,3-diaminopropane,N-heptatriacontyl-1,3=diaminopropane,N-octatriacoutyl-1,3-diaminopropane,N-nonatriacontyl-1,3-diaminopropane, N-tetracontyl-1,3-diaminopropane,

etc., and corresponding N-alkenyl-1,3-diaminopropane. Mixtures areavailable commercially, usually at lower prices, of suitable compoundsin this class and advantageously are used for the purposes of thepresent invention. One such mixture is Duomeen T which is N-tallow-1,3-diaminopropane and predominates in alkyl and alkenyl groupscontaining from 16 to 18 carbon atoms each, although the mixturecontains a small amount of groups containing 14 carbon atoms each.Another mixture available commercially is N-coco-1,3-diaminopropanewhich contains alkyl groups predominating in 12 to 14 carbon atoms each.Still another example is N-soya1,3- diaminopropane which predominates inalkenyl groups containing 18 carbon atoms per group, although it con-N-aliphatic-1,3-diaminobutanes, N-aliphatic-1,4-diaminobutanes,N-aliphatic-1,3diaminopentanes, N-aliphatic-1,4-diaminopentanes,N-aliphatic-1,5-diaminopentanes, N-aliphatic-1,3-diaminohexanes,N-aliphatic-1,4-diaminohexanes, N-aliphatic-1,5-diaminohexanes,N-aliphatic-l ,6-diaminohexanes,

etc., may be employed, but not necessarily with equivalent results.

In some cases, polyamines containing 3 or more nitrogen atoms may beemployed. Illustrative examples of such compounds includeN-dodecyl-diethylene triamine, N-tridecyl-diethylene triamine,N-tetradecyl-diethylene triamine, etc., N-dodecyl-dipropylene triamine,N-tridecyldipropylene triamine, N-tetradecyl-dipropylene triamine, etc.,N-dodecyl-triethylene tetramine, N-tridecyl-triethylene tetramine,N-tetradecyl triethylene tetramine, etc., N- dodecyl-tripropylenetetramine, N-tridecyl-tripropylene tetramine, N-tetradecyl-tripropylenetetramine, etc., N-dodecyl-tributylene tetramine, N-tridecyl-tributylenetetramine, N-tetradecyl-tributylene tetramine, etc.,N-dodecyltetraethylene pentamine, N-tridecyl-tetraethylene pentamine,N-tetradecyl-tetraethylene pentamine, etc., N-dodecyl-tetrapropylenepentamine, N-tridecyl-tetrapropylene pentamine,N-tetradecyl-tetrapropylene pentamine, etc., N-dodecyl-tetrabutylenepentamine, N-tridecyl-tetrabutylene pentamine,N-tetradecyl-tetrabutylene pentamine, etc., and corresponding N-alkenylpolyamines.

Illustrative examples of primary alkyl amines include dodecyl amine,tridecyl amine, tetradecyl amine, pentadecyl amine, hexadecyl amine,heptadecyl amine, octadecyl amine, nonadecyl amine, eicosyl amine,heneicosyl amine, docosyl amine, tricosyl amine, tetracosyl amine,pentacosyl amine, hexacosyl amine, heptacosyl amine, octacosyl amine,nonacosyl amine, triacontyl amine, hentriacontyl amine, dotriacontylamine, tritriacontyl amine, tetratriacontyl amine, pentatriacontylamine, hexatriacontyl amine, heptatriacontyl amine, octatriacontylamine, nonatriacontyl amine, tetracontyl amine, etc. Conveniently, thelong chain amines are prepared from fatty acids or more particularlymixtures of fatty acids formed as products or by-products. Such mixturesare available commercially, generally at lower prices and, ashereinbefore set forth, the mixtures may be used without the necessityof separating individual amines in pure state.

An example of such a mixture is hydrogenated tallow amine which isavailable under 'various trade names including Alamine H26D and ArmeenHTD. These products comprise mixtures predominating in alkyl aminescontalning 16 to 18 carbon atoms per alkyl group, although they containa small amount of alkyl groups hav- 60 ing 14 carbon atoms.

As hereinbefore set forth, the amine compound is reacted with anepihalohydrin compound. Epichlorohydrin is preferred. Otherepichlorohydrin compounds include 1,2-epoxy-4-chlorobutane,2,3-epoxy-4-chlorobutane, 1,2- 5 epoxy-S-chloropentane,2,3-epoxy-5-chloropentane, etc. In general, the chloro derivatives arepreferred, although it is understood that the corresponding bromo andiodo compounds may be employed. In some cases, epidihalohydrin compoundsmay be utilized. It is understood that the dif- 70 ferent epihalohydrincompounds are not necessarily equivalent and that, as hereinbefore setforth, epichlorohydrin is preferred.

The amine is reacted with the epihalohydrin compound in a mole ratio offrom 1 to 2 IllOle proportions of amine to 1 to 1.5 mole proportions ofepihalohydrin compound. The polymer will contain from 2 to 20 or morerecurring units and preferably from 3 to 10 recurrin units. In general,the diamine is reacted with epichlorohydrin in a ratio of 1 mole ofdiamine to 1.25 moles of epichlorohydrin. When a monoamine is used, themonoamine preferably is reacted with epichlorohydrin in equal moleproportions.

The reaction of amine and epihalohydrin may be effected in any suitablemanner. In one method, the desired quantity of amine and epihalohydrincompound may be charged to a reaction zone and therein reacted, althoughgenerally it is preferred to supply one reactant to the reaction zoneand then introduce the other reactant stepwise. Thus, the epihalohydrincompound may be charged to the reaction zone and the amine is addedstepwise, with stirring. Preferably, the reaction of epichlorohydrinwith the second or later portions of the amine is effected at a highertemperature than with the first portion of the amine. The reactionpreferably is effected in the presence of a suitable solvent andparticularly a hydroxylic solvent. In a preferred method, a solution ofthe amine in a solvent and a separate solution of the epihalohydrincompounds in a solvent are prepared and these solutions then arecommingled in the manner hereinbefore set forth, at least one of thesolvents being hydroxylic. Any suitable hydroxylic solvent may beemployed, a particularly suitable solvent comprising an alcoholincluding ethanol, propanol, butanol, etc., 2-propanol beingparticularly desirable. Other hydroxylic solvents comprise glycolsincluding ethylene glycol, propylene glycol, etc., glycerol and otherpolyhydric solvents.

The reaction of amine compound and epihalohydrin compound is effected atany suitable temperature, which generally will be within the range offrom about to about 300 F. and preferably is in the range of from aboutto about 200 F. Conveniently, this reaction is effected by heating anepichlorohydrin solution in dilute alcohol at refluxing conditions, withstirring, gradually adding the amine thereto, and continuing theheating, preferably at a higher temperature, until the reaction iscompleted, or the reverse order of adding the reactants may be employed.

After the initial reaction of the amine compound and epihalohydrincompound is completed, the organic halide salt which is inherentlyformed, is converted to an inorganic salt to thereby liberate the freeamine for further reaction to form the desired polymeric product. Thismay be effected in any suitable manner and generally is accomplished byreacting the primary reaction product with a strong inorganic base suchas sodium hydroxide, potassium hydroxide, etc., to form thecorresponding metal halide. The reaction to form the metal halide iseffected at a temperature within the range of from about to about 210 F.and preferably from about to about 200 F. The inorganic base preferablyis added in at least two steps, with intervening heating and reacting,so that organic halide formed after the first addition of inorganic baseis in turn reacted to liberate the free amine.

In one embodiment, the product at this stage of manufacture may bewithdrawn from the reaction zone and filtered or otherwise treated toremove the inorganic halide. Generally, however, it is preferred toperform the next step in the same reaction zone without removing theinorganic halide. At the conditions used in forming the polymericreaction product, the inorganic halide is inert and, therefore, itspresence is not objectionable. Regardless of whether or not theinorganic halide is removed, the primary reaction product of the aminecompound and epihalohydrin compound is now further heated and reacted inorder to form the desired linear polymeric reaction product. Thisfurther heating and reacting is at a temperature of from about 130 toabout 210 and preferably from about 165 to about 200 F.

After formation of the desired polymeric reaction product or before thisstep as mentioned above, the inorganic halide salt is removed in anysuitable manner, including filtering, centrifugal separation, etc. Insome cases, it may be of advantage to elfect the filtration at anelevated temperature, which may range from about 100 to about 160 F. ormore.

As hereinbefore set forth, the polymeric reaction prodnot will have from2 to 20 and preferably from 3 to 10 recurring units. The reactionproducts will range from liquids to solids and, when desired, may beprepared as a solution in a suitable solvent for ease of handling anduse. A preferred solvent is an aromatic hydrocarbon including benzene,toluene, xylene, ethylbenzene, diethylbenzene, cumene, etc., or a mixedsolvent such as naphtha, kerosene, xylene tower bottoms, etc. In oneembodiment, all or a portion of the aromatic solvent desired in thefinal product may be used as a solvent during the reaction. In additionto the hydroxylic solvent, the aromatic solvent is allowed to remain inthe final product.

.As hereinbefore set forth, in a preferred embodiment the polymericreaction product is formed as a solution in both an aromatic solvent anda parafiin oil. The aromatic solvent may be selected from thosehereinbefore set forth and, for economical reasons, preferably comprisesa mixed aromatic product as, for example, xylene tower bottoms, whichgenerally are available at lower cost. Any suitable parafiin oil is usedas the other solvent and generally will have an API gravity of aboveabout 20 and a SUS viscosity at 100 F. of between 80 and 120 seconds.The solution of polymeric reaction product to be added to thelubricating oil may comprise from about 5% to about 20% and preferablyfrom about 6% to about 15% by weight of the polymeric reaction productactive ingredient, from about 5% to about 20% and preferably from about6% to about 15% by weight of the aromatic solvent and from about 60% toabout 90% and preferably from about 70% to about 88% by weight of theparafiin oil. It is understood that these concentrations areillustrative and that higher or lower concentrations of these componentsmay be used when advantages appear therefor.

The polymeric reaction product is incorporated in the lubricating oil ina sufficient concentration to provide the desired lubricity and enginecleanliness. The concentration may range, on the basis of polymericreaction product active ingredient, from about 0.5% to about 10% andpreferably from about 1% to about 5% by weight of the lubricating oil.Accordingly, the amount of final solution to be used will be sufficientto introduce the polymeric reaction product active ingredient in a concentration hereinbefore set forth.

It is understood that the polymeric reaction product may be used alongwith other additives which normally are incorporated in lubricating oilincluding, for example, one or more of viscosity index improvers, pourpoint depressants, oxidation inhibitors, rust inhibitors, anti-foamingagents, extreme pressure additives, metal deactivators, etc. Theadditional additives will be selected with regard to the compatibilitythereof with the polymeric reaction product and preferably are used inconventional concentrations.

The polymeric reaction product is used in any lubricating oil which issuitable for use in the two-cycle or rotary engine including the Wankelengine. In general, the lubricating oil will be available from thosemarketed commercially and preferably is of the SAE 30 lubricating oilviscosity. It is recognized that the lubricating oil for use in thetwo-cycle or rotary engines may differ somewhat from those normally usedin other engines. Accordingly, special lubricating oils are marketed forsuch use by many of the oil companies and the particular lubricating oilwill be selected with regard to the manufacturers recommendations.Similarly, any suitable gasoline or other fuel,

including alcohol or gasoline-alcohol mixtures, may be used. In mostcases, the generally available gasoline is utilized for this purpose andcomprises conventional gasoline boiling within the range of from about75 to about 400 F., more or less, and comprises a mixture ofhydrocarbons. The gasoline may contain conventional additives, includingoxidation inhibitor, metal deactivator, detergent, dye, etc., andtetra-alkyl lead or other anti-knock agent. However, the trend is toeliminate lead from the gasoline and such elimination may cause otherproblems in the operation of the engine, which problems are minimized bythe novel method of the present invention. The gasoline and lubricatingoil will be used in any suitable proportions and may be within thefuelzlubricating oil ratios of from 20:1 to 150:1, although higher orlower ratios may be used when advantages appear therefor.

The following examples are introduced to illustrate further the noveltyand utility of the present invention but not with the intention ofunduly limiting the same.

EXAMPLE I A polymeric reaction product is prepared by the reaction ofone mole proportion of epichlorohydrin with one mole proportion ofhydrogenated tallow amine. It will be noted that the hydrogenated tallowamine comprises a mixture which predominates in alkyl amines containing16 to 18 carbon atoms per alkyl group, although they contain a smallamount of alkyl groups having 14 carbon atoms. The reaction is eflectedsubstantially by first forming a solution of 2 moles of epichlorohydrinin 600 cc. of a solvent mixture comprising 400 cc. of Xylene and 200 cc.of 2-propanol. A separate solution of 2 moles of the hydrogenated tallowamine is prepared in an equal volume of xylene. 'One mole of the lattersolution is gradually added to the epichlorohydrin solution withstirring and heating at 130-140 F. for about 2.5 hours, after whichanother mole of the hydrogenated tallow amine is added gradually to thereaction mixture, stirred and reacted at 175 F. for about 2.5 hours. Onemole of sodium hydroxide then is added with stirring and heating at 185-200 F. for 3 /2 hours, after which another mole of sodium hydroxide isadded to the mixture, stirred and reacted at 185-200 F. for about 1hour.

It will be seen that the heating and reacting after the addition of thesodium hydroxide and concomitant liberation of the free amine results inthe formation of the desired polymeric reaction product. 'Followingcompletion of the reaction, the mixture is cooled, filtered and thefiltrate then is distilled to remove the alcohol.

In this preparation at least part and preferably all of the xylenesolvent is allowed to remain and the concentration of xylene solvent isadjusted to form a solution containing the active ingredient in aconcentration of 60% by weight. The resulting solution then iscommingled with a parafiin oil having an API gravity of 23 in aproportion of 1 part by weight of the polymeric reaction productsolution to 4.5 parts by weight of the paraflin oil.

However, for analytical purposes, a portion of the xylene solution isdistilled at 0.1 mm. of vacuum to remove the xylene and to recover asubstantially pure reaction product. This product is a white tooff-white hard, brittle solid, and has a softening point of about F. andmelts at F. to a dark yellow liquid, which liquid is soluble in allcommon hydrocarbons and other organic solvents. This product has anequivalent weight by titration with acid of 334.

EXAMPLE II It will be noted that in Example I the first mole of tallowamine is reacted with epichlorohydrin at l30-140 F. and then the secondmole of tallow amine is reacted at the higher temperature of F. Wheneffecting the reaction in this manner, the polymeric product will have atotal of about 12 recurring units. However, when the reaction isetfected at substantially the same temperature,

the reaction product will contain or less recurring units. A specificpreparation was calculated to comprise 4 recurring units and a molecularweight of about 1400.

The polymeric reaction product is commingled with a heavy aromaticnaphtha to form a solution containing the polymeric reaction productactive ingredient in a concentration of 40% by weight. The resultingsolution then is commingled with a heavy parafiinic naphtha in a weightratio of 1 part polymeric reaction product solution to 3 parts by weightof the parafiinic naphtha.

EXAMPLE III The polymeric reaction porduct of this example is preparedby the reaction of 1 mole proportion of Duomeen T and 1.25 moleproportions of epichlorohydrin. As hereinbefore set forth, Duomeen T isN-tallow-1,3-diaminopropane and predominates in aliphatic groupscontaining 16 to 18 carbon atoms. The reaction is effected by charging150 grams of epichlorohydrin, 100 grams of isopropyl alcohol and 15grams of xylene into a reaction vessel and raising the temperature toabout 115 F. Then 180 grams of Duomeen T and 135 grams of xylene aresupplied to the reaction vessel, while maintaining the temperature atabout 120 F. The reaction vessel then is heated to 165 F. and maintainedat this temperature for 4 hours, after which the remaining amine (180grams) and 135 grams of xylene are supplied to the reaction vessel andthen heated for 4 hours. Following this primary reaction, 34 grams ofsodium hydroxide are added gradually to the reaction vessel which isheated to 185 F. and maintained at this temperature for 4 hours, afterand comprises a high aromatic (38%) no lead fuel. The lubricating oilcomprised a mixture of by weight neutral oil and 10% by weight of brightstock and was formulated to simulate a SAE 30 lubricating oil. Theevaluation was made in the Falex machine. This procedure is described indetail in a book entitled Lubricant Testing authored by E. G. Ellis andpublished by Scientific Publications (Great Britain) Limited, 1953,pages 150-154. Briefly. the Falex machine consists of a rotating pinwhich runs between two V-shape bearings which are spring loaded againstthe pin and provided with means for varying the load. The sample to betested is poured into the metal trough in which the pin and bearings arepartly submerged. In these evaluations, the test procedure consisted ofan initial load of 200 pounds for 5 minutes, then increasing the load to250 pounds for 5 minutes, and then the load is increased by poundincrements for 5 minutes each until seizure occurs. At each loadincrease the torque in pounds per square inch at each load andtemperature are reported.

The following table reports the results of evaluations made using theIndolene alone with no added lubricating oil (Run No. 1), theIndolene-lubricating oil mixture containing 10% by weight of acommercial lubricating oil additive (Run No. 2), theIndolene-lubricating oil mixture containing 10% by weight of a differentcommercial lubricating oil additive (Run No. 3), and theIndolenelubricating oil mixture containing 10% by weight of the solutionprepared as described in Example HI (Run No. 4). These results arereported in the following table.

TABLE I R Torque Temperature, F.

Seizure occurred in less than 5 minutes at the maximum load. The sampleevaporated while running. No

additional sample was added.

which 17 grams of sodium hydroxide are added gradually to the reactionvessel and maintained at F. for another 4 hours. Here again, it will beseen that the continued reaction at the elevated temperature after theaddition of sodium hydroxide serves to effect polymerization of theprimary reaction product because of the liberation of the free amine.Following the reaction, the vessel is cooled and the products arefiltered to remove the inorganic halide salt and the filtrate then isdistilled to remove the isopropyl alcohol solvent.

The polymeric reaction product then is formed as a 50% by weight activeingredient solution in xylene tower bottoms. The resulting solution thenis commingled in a proportion of 1 part by weight thereof with 4 partsby weight of a paraffin oil available commercially as Shell Carnea Oil21. This oil is said to have an API gravity of 21 minimum, an ASTM colorof 2 maximum, a pour point of less than 15 F. maximum, a Cleveland OpenCup flash point of 310 F. and a SUS viscosity at 100 F. of 90- 110 andat 210 F. of 37-40.

EXAMPLE IV The solution prepared as described in Example HI wasevaluated as an additive in a fuel-lubricating oil mixture in a weightratio of fuel to lubricating oil of 80: 1. The fuel used in this exampleis available commercially as Indolene From the data in the above table,it will be seen that the Indolene alone (Run No. 1) underwent seizure ata load of 625 pounds. For the blend of gasoline and lubricating oil, itappears that the commercial additives for conventional lubricating oilswere of no benefit and actually resulted in seizure at a lower load(Runs Nos. 2 and 3). In contrast to the above, the solution of polymericreaction product prepared as described in Example III served to increasethe load to 875 pounds (Run No. 4).

EXAMPLE V The solution of polymeric reaction product in the heavyaromatic and heavy parafiinic naphthas, prepared as described in Example11,. is commingled in a concentration of 8% by weight in a lubricatingoil for use in admixture with gasoline in a gasoline to lubricating oilweight ratio of 100:1. The resulting mixture is used as charge to thecombusion chamber of a spark ignited rotary engine.

I claim as my invention:

1. A lubricating oil-fuel mixture for two-cycle or rotary enginescontaining, as an additive to improve lubricity and engine cleanliness,the polymeric reaction product, formed at a temperature of from about 70to about 300 F., of from about 1 to 2 mole proportions of a primary orsecondary aliphatic amine of from about 12 to about 40 carbon atoms withfrom about 1 to about 1.5 mole proportions of an epihalohydrin compoundselected from the group consisting of epichlorohydrin,1,2-epoxy-4-chlorobutane, 2,3-epoxy-4-chlorobutane, and2,3-epoxy-5-chloropentane and corresponding bromo and iodo compounds.

2. The lubricating oil-fuel mixture of claim 1 containing said polymericreaction product in a concentration of from about 0.5% to about 10% byweight of the lubricating oil.

3. The lubricating oil-fuel mixture of claim 1 in which said amine is aprimary amine containing from about 12 to about 40 carbon atoms.

4. The lubricating oil-fuel mixture of claim 1 in which said amine is anN-aliphatic-alkylene polyamine containing from about 12 to about 40carbon atoms in a said aliphatic.

5. The lubricating oil-fuel mixture of claim 4 in which said amine isN-tallow-1,3-diaminopropane.

6. The lubricating oil-fuel mixture of claim 1 in which saidepihalohydrin compound is epichlorohydrin.

7. The lubricating oil-fuel mixture of claim 1 in which said polymericreaction product is prepared as a solution in both an aromatic solventand a paraflinic solvent.

References Cited UNITED STATES PATENTS 3,017,358 l/ 1962 Pollitzer252--51.5 R 3,189,652 6/ 1965 Pollitzer 4472 3,251,852 5/1966 De Grooteet al. 25251.5 R 3,296,133 1/ 1967 Ratner et al. 252-515 A 3,373,1113/1968 Le Suer et al 252-515 A 3,705,109 12/ 1972 Hausler et al. 252-515A DANIEL E. WYMAN, Primary Examiner A. P. DEMERS, Assistant Examiner US.Cl. X.R.

